Winchester County VA Homes for Sale

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  /35

  $337,000

  • 3 Beds
  • 4 Baths
  • 1,320 Sq Ft

  124 Worsham Terrace, Winchester, VA 22602

  Welcome to this beautifully maintained townhouse that offers the perfect blend of comfort, style, and convenience. Boasting an attractive full brick-front exterior with classic black shutters, this home offers timeless curb appeal and a welcoming first impression. The private driveway, attached one-car garage, and well-maintained landscaping add both functionality and charm. The main living level

  

  David Peña

  Corcoran McEnearney

  124 Worsham Terrace, Winchester, VA 22602
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  /3

  $425,000

  $20K PRICE DROP

  • 6 Beds
  • 3 Baths
  • 1,917 Sq Ft

  623 Smithfield Ave, Winchester, VA 22601

  Spacious split-foyer home in the heart of Winchester featuring 6 bedrooms and 3 full bathrooms,. Well-maintained and located in a convenient neighborhood with no HOA.

  

  Carlos Soares

  Samson Properties

  623 Smithfield Ave, Winchester, VA 22601
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  /26

  $369,000

  • 3 Beds
  • 2.5 Baths
  • 1,737 Sq Ft

  614 Sherlock Trace, Winchester, VA 22601

  **Excellent Opportunity in the Heart of Winchester!** Don't miss the chance to own a well-located home in one of Winchester's most convenient areas. Situated on a quiet street, this property offers easy access to shopping, dining, schools, parks, and major commuter routes—everything that matters is just minutes away. Featuring **3 bedrooms** plus **two additional versatile rooms**, this home

  

  Carlos Soares

  Samson Properties

  614 Sherlock Trace, Winchester, VA 22601
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  /4

  $289,900

  Coming Soon

  • 2 Beds
  • 1 Bath
  • 1,458 Sq Ft

  102 N Purcell Ave, Winchester, VA 22601

  Charming home ideally located just minutes from the heart of historic Winchester! Whether you're looking for convenient access to shopping, dining, entertainment, or commuter routes, this home offers an exceptional location paired with valuable updates for peace of mind. Relax on the inviting covered front porch, the perfect place to enjoy your morning coffee or unwind at the end of the day. The

  

  Bradley Comstock

  ERA Oakcrest Realty, Inc.

  102 N Purcell Ave, Winchester, VA 22601
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  /11

  $1,499,000

  • Land
  • 2.45 Acres
  • $611,837 per Acre

  821,829,839, and 851 Fox Dr, Winchester, VA 22603

  Location Location Location! 2.45 Acres comprised of 4 Lots with 3 income producing dwellings. Site falls withing the Frederick County Comprehensive Plan for Commercial Uses. Located just off the Route 37 and Route 522 Interchange next to Sheetz and KFC. All Dwellings and Outbuildings are strictly as-is.

  

  Jim Shebest

  Coldwell Banker Realty

  821,829,839, and 851 Fox Dr, Winchester, VA 22603
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  /23

  $350,000

  $25K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 1,916 Sq Ft

  317 N Kent St, Winchester, VA 22601

  Step into a world of timeless elegance and modern luxury with this stunning Colonial residence, beautifully renovated in 2015 while preserving its historic charm. Nestled in a serene setting, this detached home offers a perfect blend of classic architecture and contemporary comforts, making it an ideal retreat for those seeking an exclusive lifestyle. As you enter, you are greeted by rich

  

  Clark Smith

  Samson Properties

  317 N Kent St, Winchester, VA 22601
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  /27

  $359,900

  • 3 Beds
  • 2 Baths
  • 1,743 Sq Ft

  601 Gray Ave, Winchester, VA 22601

  Welcome to Gray Avenue! This beautifully updated 3-bedroom, 2-bath home offers over 1,700 square feet of stylish living space, blending timeless charm with modern finishes throughout. Rich hardwood floors flow throughout the home, creating warmth and character from the moment you step inside. The sun-filled living room feels bright and inviting, highlighted by a custom light fixture and a

  

  Walther Vasquez Johnson

  Samson Properties

  601 Gray Ave, Winchester, VA 22601
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  /9

  $1,300,000

  • Land
  • 64.91 Acres
  • $20,028 per Acre

  Lot 7 Cedar Creek Grade, Winchester, VA

  Rare opportunity to own 64+ scenic acres on the desirable west side of Winchester, VA. This preservation parcel offers one building right and features a beautiful mix of open land and partial woodland, providing both usability and privacy. Formerly an apple orchard, the property is well suited for a small farm, specialty crops, or vineyard, with potential for additional uses with an approved

  

  Lori Bales

  Keller Williams Realty

  Lot 7 Cedar Creek Grade, Winchester, VA
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  /32

  $449,000

  • 4 Beds
  • 4.5 Baths
  • 1,913 Sq Ft

  315 National Ave, Winchester, VA 22601

  Fully reimagined for modern living while preserving its timeless charm, this stunning 1910 home in the heart of Downtown Winchester offers the perfect blend of character, luxury, and value. Completely renovated from top to bottom, every detail has been thoughtfully updated—delivering the feel of new construction within a classic architectural setting.This spacious residence features 4

  

  Carlos Soares

  Samson Properties

  315 National Ave, Winchester, VA 22601
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  /13

  $274,999

  • 2 Beds
  • 2.5 Baths
  • 1,080 Sq Ft

  206 Kimberly Way, Winchester, VA 22601

  Beautifully remodeled 2-bedroom, 2.5-bath townhouse that's ready for you to move right in! This home features a stunning updated kitchen with granite countertops and stainless steel appliances, along with modern finishes throughout. Major improvements include a new roof and heat pump installed in 2023, providing added comfort and peace of mind. Spacious living areas, updated bathrooms, and

  

  Frank Armstrong, IV

  Colony Realty

  206 Kimberly Way, Winchester, VA 22601
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  /2

  $175,000

  • Land
  • 16,117 Sq Ft
  • $472,973 per Acre

  719 Kennedy Dr, Winchester, VA 22601

  Vacant Lot in Rolling HillsOne of the last opportunities to own a vacant lot in the desirable Rolling Hills community. This property offers the perfect setting to build your new home or presents an excellent opportunity for a long-term investment. Enjoy a well-established neighborhood with limited remaining buildable lots. Buyer to verify zoning, utilities, and intended use. Water and Sewer

  

  Frank Armstrong, IV

  Colony Realty

  719 Kennedy Dr, Winchester, VA 22601
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  /40

  $324,000

  $25K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 1,996 Sq Ft

  802 E Cork St, Winchester, VA 22601

  Motivated Seller! Check out the Virtual Tour! Rich with character and steeped in history, this spacious vintage home sits proudly on a corner lot, offering timeless appeal with many original features still intact. From the moment you enter, you’ll appreciate the craftsmanship of a bygone era—complete with built-in bookshelves, a charming upper-level sleeping porch, and a traditional canning

  Jennifer Egen Samson Properties

  802 E Cork St, Winchester, VA 22601
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  /12

  $80,000

  • Land
  • 5,662 Sq Ft
  • $615,385 per Acre

  520 Highland Ave, Winchester, VA 22601

  Empty lot ready to build a home one. The lot is fully fenced with front and rear gates. The front of the lot meets the sidewalks and road of Highland Ave. The rear of the lot meets a gravel alley way that could give access to off street parking on this lot. Homes in the city are in demand, so don't miss this opportunity. Zoned HR-1Can only be used for single family dwellingsFront setback:

  Michael Sprague Samson Properties

  520 Highland Ave, Winchester, VA 22601
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  /11

  $80,000

  • Land
  • 3,484 Sq Ft
  • $1,000,000 per Acre

  24 N Pleasant Valley Rd, Winchester, VA 22601

  Ready for building! Clear open lot that is ready for a home to be built. Winchester City is the fastest growing city in the state and homes are in high demand. Don't miss your opportunity. Property has road front access as well as a gravel alley in the rear that could be used for access to off street parking.Zoned MR - medium density residential districtCan only be used for single family

  Michael Sprague Samson Properties

  24 N Pleasant Valley Rd, Winchester, VA 22601
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  /22

  $269,000

  • Land
  • 42,253 Sq Ft
  • $277,320 per Acre

  823 Armistead St, Winchester, VA 22601

  *** Price shown is for lot only. Seller is willing to assist Buyer in building this beautiful home plandesigned by Seller customized for this lot and optimized for cost effective construction. Closingon the lot may occur upon issuance of the Building Permit in Buyer’s name by the City ofWinchester. ***This modern farmhouse style home includes 5,630 square feet of living space

  Janet Flaherty Keller Williams Realty

  823 Armistead St, Winchester, VA 22601
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  /33

  $455,000

  $5K PRICE INCREASE

  • 3 Beds
  • 2.5 Baths
  • 1,440 Sq Ft

  310 Longview Ave, Winchester, VA 22601

  THIS IS A MUST SEE! Huge price reduction from motivated seller. OPEN HOUSE THIS SUNDAY.Amazing, location, 3 years new property, located in short drive to everything, Winchester. This is an offering you don't want to miss out on. Its not often that a nearly new construction home with all the best of everything comes on the market. For starters theres No HOA .All the appliances and operating

  Dave Milburn Coldwell Banker Realty

  310 Longview Ave, Winchester, VA 22601
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  /51

  $390,000

  $10K PRICE DROP

  • 5 Beds
  • 2 Baths
  • 1,011 Sq Ft

  605 Dunlap St, Winchester, VA 22601

  Priced to reflect the need for some updating, this home offers opportunities and personalization while remaining move-in ready 1011sf total living space.This home is in very good shape. The sellers are selling this property completely As-IS. NO HOA Perfectly home on a quiet lot embraced by mature, stately trees, this 5-bedroom, 2 full-bathroom home offers both seclusion and incredible

  Alexandra Brown Spring Hill Real Estate, LLC.

  605 Dunlap St, Winchester, VA 22601
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  /103

  $899,000

  • 3 Beds
  • 3.5 Baths
  • 3,497 Sq Ft

  466 Merrimans Ln, Winchester, VA 22601

  Your long search is over! Beautifully renovated all-brick ranch home situated on a secluded 2.03-acre lot in the city of Winchester, just a short walk to Valley Health. Offering an exceptional combination of privacy, convenience, and quality. This home features spacious living areas, three fireplaces, including one in the primary bedroom.The finished lower level provides outstanding

  John Schroth Colony Realty

  466 Merrimans Ln, Winchester, VA 22601
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  /5

  $295,000

  Coming Soon

  • 3 Beds
  • 1 Bath
  • 913 Sq Ft

  405 Shenandoah Ave, Winchester, VA 22601

  Ideally situated just minutes from I-81 and a short drive to historic Old Town Winchester, this centrally located rambler offers both convenience and investment potential. Situated on a desirable corner lot, the property features a fenced yard and a storage shed for added functionality. The home has been recently refreshed with new paint and landscaping, providing excellent curb appeal and a

  Heloisa Amar Samson Properties

  405 Shenandoah Ave, Winchester, VA 22601
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  /47

  $379,990

  $10K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 2,102 Sq Ft

  519 Fairmont Ave, Winchester, VA 22601

  Expect a long love affair with this home.Some homes feel like they were built with patience, pride, and a sense of permanence—and this historic Winchester beauty has that feeling the moment you step inside. Set near Old Town Winchester and positioned right next to the approved Cider Hill Neighborhood Design District, it offers something rare: preserved historic character today, with a

  Hannah Won Samson Properties

  519 Fairmont Ave, Winchester, VA 22601
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  /52

  $425,000

  • 2 Beds
  • 2 Baths
  • 1,799 Sq Ft

  437 Beechcroft Rd, Winchester, VA 22601

  BRICK BEAUTY ON A CORNER LOT WITH AN ATTACHED CARPORT AND A FULL BASEMENT. This remodeled and freshly painted 2-bedroom, 2-bath rancher with newly refinished hardwood floors is move-in ready. In-town convenience with nearby shopping, restaurants and services. A short drive to commuter routes 81, 37 and 50, downtown and Winchester Medical Center. Perfect for those who are downsizing or just

  Teresa Strohmeyer ERA Oakcrest Realty, Inc.

  437 Beechcroft Rd, Winchester, VA 22601
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  /57

  $595,000

  $100K PRICE DROP

  • 5 Beds
  • 3 Baths
  • 2,182 Sq Ft

  813 Chelsea Dr, Winchester, VA 22601

  BEAUTIFUL NEW PRICE FOR A BEAUTIFUL HOUSE! ELEGANT AND SPECTACULAR! DRAMATIC SHOW STOPPER HOME IN MEADOW BRANCH SOUTH. If your passion is entertaining and fine living, this well-appointed, custom-built home is for you! Open floor plan with cathedral and multi-tiered tray ceilings, arches and plantation shutters. Fresh paint and newly refinished hardwood floors. In-town convenience near shopping,

  Teresa Strohmeyer ERA Oakcrest Realty, Inc.

  813 Chelsea Dr, Winchester, VA 22601
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  /26

  $364,990

  New Construction $3K PRICE DROP

  • 3 Beds
  • 3.5 Baths
  • 1,756 Sq Ft

  11 Monteith Dr, Winchester, VA 22601

  3 Level Townhome with Lower Level Bathroom! This beautifully upgraded home features an open-concept layout with spacious living areas and a stunning kitchen complete with oversized island seating for four; perfect for entertaining and everyday living. The third level offers conveniently located laundry near the bedrooms for added convenience. Enjoy outdoor living on the 10x16 maintenance-free

  DRB Homes Builder

  11 Monteith Dr, Winchester, VA 22601
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  /48

  $525,000

  $20K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 2,317 Sq Ft

  938 Wayne Dr, Winchester, VA 22601

  Improved Price!! Welcome to this spacious and well-maintained home in the desirable Meadow Branch South community. Offering over 3,300 square feet, this 4-bedroom, 2.5-bath home provides the perfect blend of space, comfort, and thoughtful updates. The main level features an updated kitchen, ideal for both everyday living and entertaining, along with multiple living areas that offer flexibility

  Kira Grubb Realty ONE Group Old Towne

  938 Wayne Dr, Winchester, VA 22601
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  /41

  $379,900

  $20K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,405 Sq Ft

  1851 Melvor Ln, Winchester, VA 22601

  Extremely well-maintained 2-bedroom, 2-bath Ranch home in the desirable Willow Lawn Cottages 55+ community. This main-level living home features an open floor plan, vaulted ceiling, solar tubes for natural light, and a cozy gas fireplace in the living room. The primary suite offers a private bath, while a bright Florida room provides additional space for relaxing or entertaining. Step outside to

  RoxAnn Grimes RE/MAX Roots

  1851 Melvor Ln, Winchester, VA 22601
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  /46

  $1,150,000

  • 5 Beds
  • 5 Baths
  • 5,695 Sq Ft

  801 Armistead St, Winchester, VA 22601

  There are homes that simply provide shelter. And then there are homes like this—homes that make you slow down, take a deep breath, and picture the life you've been working so hard to create. Nestled in one of Winchester's most beloved neighborhoods, this stately residence blends timeless elegance with the confidence that comes from knowing the important work has already been done. Over the past

  Donna Chong Samson Properties

  801 Armistead St, Winchester, VA 22601
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  /3

  $425,000

  • 4 Beds
  • 3 Baths
  • 2,157 Sq Ft

  1709 Brandon Dr, Winchester, VA 22601

  Spacious Home in a Prime Location! Discover the potential of this well-built Cape Cod offering generous living spaces and timeless charm. The welcoming living and dining area features a cozy fireplace, creating the perfect setting for gatherings and everyday living. The main level includes a desirable primary suite with a private full bath, an additional bedroom, and a hall bath for added

  Darcy Amburn Colony Realty

  1709 Brandon Dr, Winchester, VA 22601
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  /55

  $299,990

  $11K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,474 Sq Ft

  406 Highland Ave, Winchester, VA 22601

  HERE IS YOUR CHANCE! BACK ON THE MARKET DUE TO NO FAULT OF THE SELLERS!!DIRECTIONS FOR PARKING; FROM NAT AVE TAKE RIGHT ON ATHEY ALLY TO 4 CAR PARKING AREA ON LEFT - LOOK FOR 406 MARKER. Located in The Historic Old Town Winchester area with private parking right off of Athey Alley, we are happy to list this nicely remodeled 2 story circa 1930s, center hall home.. Since the purchase of this

  Lisette Turner Century 21 Redwood Realty

  406 Highland Ave, Winchester, VA 22601
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  /36

  $320,000

  • 3 Beds
  • 3 Baths
  • 1,281 Sq Ft

  115 S Purcell Ave, Winchester, VA 22601

  Don't miss this 3-bedroom, 3 full-bath bungalow in a prime location! Just minutes from vibrant downtown shopping and dining, and a short walk to Jim Barnett park. The park includes a dog park, swimming pool, and pickleball courts. This home offers the ideal combination of convenience, charm, and access to outdoor amenities. New roof installed in 2018. Great investment opportunity! Currently

  Matthew Berry MarketPlace REALTY

  115 S Purcell Ave, Winchester, VA 22601
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  /17

  $199,900

  $15K PRICE DROP

  • Land
  • 15,681 Sq Ft
  • $555,278 per Acre

  506 Fairmont Ave, Winchester, VA 22601

  NEW CITY LOT! This newly configured lot in the heart of downtown Winchester has been expanded and is ready for you to build your dream home. Featuring a width of approximately 100 feet, you have plenty of space to accommodate nearly any home of your choice. As a bonus, the driveway will be on the neighboring lot, which allows even more buildable space. Additionally, you do not have to worry about

  Dan Whitacre Colony Realty

  506 Fairmont Ave, Winchester, VA 22601
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  /39

  $449,900

  • 2 Beds
  • 2 Baths
  • 2,370 Sq Ft

  443 Fairmont Ave, Winchester, VA 22601

  So much potential !!! Great location, private yard, lots of square feet. Lot is 3/4 acre !Needs TLC. Listed $120,000 under tax assessment to allow room for updating. Kitchen has Corion counter tops , great cabinets. Very large room with beautiful book case built in, has fantastic screened in porch, Very large ( 24 X 24 ) family room with fireplace .

  Jeff Webber Long & Foster Real Estate, Inc.

  443 Fairmont Ave, Winchester, VA 22601
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  /36

  $385,000

  $14K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,601 Sq Ft

  13 E Leicester St, Winchester, VA 22601

  Incredible location, incredible home! Relax on the elevated front porch overlooking Leicester St, or retreat to the private back yard. Inside, gleaming wood floors and original trim compliment the new kitchen and bathrooms. HVAC, wiring, plumbing, windows, roofing, and siding have been lovingly replaced/updated in the last 5 years. This home is walkable to everything, and sits on a calm side

  William Steinmetz RE/MAX Roots

  13 E Leicester St, Winchester, VA 22601
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  /96

  $489,900

  • 5 Beds
  • 3 Baths
  • 1,887 Sq Ft

  419 Summit Ave, Winchester, VA 22601

  Welcome Home! This beautifully renovated single-family home offers everything you need and more. Featuring hardwood floors throughout the main level, custom cabinets, and granite countertops in the kitchen, this home combines style and functionality. A new roof adds peace of mind, and the fully finished lower level provides additional living space for relaxation or entertainment. With 5 spacious

  Waqas Abbasi Lifestyle Realty, LLC.

  419 Summit Ave, Winchester, VA 22601
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  /28

  $400,000

  $29K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 1,432 Sq Ft

  115 E Monmouth St, Winchester, VA 22601

  Welcome to this 2 level house, the spacious patio backyard will be the perfect spot to relax and enjoy a relaxing day. Located near multiple stores and parks. Schedule your showing today!

  Mafe Zambrano Inmobiliaria De Las Casas LLC

  115 E Monmouth St, Winchester, VA 22601
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  /33

  $399,000

  $26K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 2,100 Sq Ft

  1025 S Loudoun St, Winchester, VA 22601

  TONS OF UPGRADES! This home has been updated top to bottom. From the roof, windows, kitchen, bathrooms, light fixtures, HVAC, and so on. Located just 1 block from Handley High School, this home and all of its high end improvements make it a treasure waiting to be discovered. As you walk through this home you'll notice that a ton of care and thoughtfulness was put into what it is today. The

  Michael Sprague Samson Properties

  1025 S Loudoun St, Winchester, VA 22601
• 

  

  /15

  $378,690

  New Construction

  • 4 Beds
  • 3.5 Baths
  • 1,889 Sq Ft

  1809 Sloane St, Winchester, VA 22601

  1809 Sloane St. is an attractive new 3 level townhome with full brick front in Winchester, VA for August move-in. Included Deck for first 3 homebuyers! Our modern Adams floorplan features a 1-car garage, and a bedroom and full bathroom on the first floor. The main level with LVP Floors features a kitchen equipped with beautiful Quartz countertops, white cabinets, and stainless-steel appliances.

  D.R. Horton Builder

  1809 Sloane St, Winchester, VA 22601
• 

  

  /10

  $399,000

  • Land
  • 3,920 Sq Ft
  • $4,433,333 per Acre

  1 N Braddock St, Winchester, VA 22601

  Make Offer! Excellent Development Opportunity! Downtown Winchester, VA! APPROVED (!) Mixed Use site plan for multi-story building consisting of 1st floor commercial space (1,340 SF) with 6x spacious luxury condos/apartments (potential for seven) with rooftop patio above (for total of 8 rental units)! Legacy development opportunity! One North is located in the second historical district and

  Gillian Greenfield Coldwell Banker Premier

  1 N Braddock St, Winchester, VA 22601
• 

  

  /30

  $385,000

  • 3 Beds
  • 1 Bath
  • 1,280 Sq Ft

  540 Bellview Ave, Winchester, VA 22601

  Charming rambler just minutes from historic Old Town Winchester with convenient access to I-81, making commuting simple and stress-free. This inviting home features beautiful hardwood floors, a spacious living room with a cozy fireplace, and a formal dining room perfect for hosting family and friends. The kitchen offers easy access to the backyard, creating a seamless flow for indoor-outdoor

  Heloisa Amar Samson Properties

  540 Bellview Ave, Winchester, VA 22601
• 

  

  /31

  $560,000

  • 4 Beds
  • 3 Baths
  • 2,068 Sq Ft

  110 Russelcroft Rd, Winchester, VA 22601

  Nestled in the established Cedarmeade community, this beautifully updated 4-bedroom, 3-bath ranch home offers the perfect combination of comfort, style, and functionality. With over 2,000 square feet of finished living space, this home is designed to accommodate both everyday living and effortless entertaining. Step inside to find warm hardwood flooring, abundant natural light, and thoughtfully

  Grace Mooney Coldwell Banker Premier

  110 Russelcroft Rd, Winchester, VA 22601
• 

  

  /45

  $449,000

  $56K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 2,293 Sq Ft

  3137 Eton Place, Winchester, VA 22601

  Welcome to The Lofts at Creekside! Better than new and absolutely breathtaking, this four-level interior townhome delivers style, space, and an unbeatable lifestyle—all within walking distance to top-rated restaurants, shopping, and the historic Kernstown Battlefield. Offering 3 bedrooms and 2.5 baths, the home features a chic upper-level loft that opens to a stunning private terrace, perfect for

  Laura White ERA Oakcrest Realty, Inc.

  3137 Eton Place, Winchester, VA 22601

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